Abstract
Primary and secondary a- halomethyl diazoketones generated via Arndt- Eistert chem. with min. loading of diazomethane efficiently alkylate arom. amines in the presence of calcium oxide to furnish the corresponding a- arylamino diazoketones under full chemocontrol. Such a simple inorg. acid scavenger fully neutralizes the hydrohalic acid formed during the nucleophilic displacement which otherwise would immediately react to produce the corresponding a- haloketone. The methodol. can be further exploited in analogous acylation- type processes on secondary arylamino diazoketones. In depth spectroscopic (1H, 13C and 15N- NMR) and crystallog. analyses document interesting structural features of these previously unknown diazo derivs.
Original language | English |
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Pages (from-to) | 4336-4347 |
Number of pages | 12 |
Journal | The Journal of Organic Chemistry |
Volume | 83 |
Issue number | 8 |
Early online date | 16 Mar 2018 |
DOIs | |
Publication status | Published - Apr 2018 |
Austrian Fields of Science 2012
- 104015 Organic chemistry
- 104026 Spectroscopy
- 301207 Pharmaceutical chemistry
- 105113 Crystallography
Keywords
- AMINO-ACIDS
- ASYMMETRIC-SYNTHESIS
- CHEMISTRY
- CONTINUOUS-FLOW SYNTHESIS
- DIAZO-COMPOUNDS
- GENERATION
- KETONES
- NUCLEAR-MAGNETIC-RESONANCE
- ORGANIC-SYNTHESIS
- STEREOSELECTIVE-SYNTHESIS